Water → 4-Chloro-2-(3-thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

HRID 55122ノート

反応式

HRID 55122 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([O:22][CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[N:16]=1.O>CN(C)C(=O)C>[Cl:21][C:19]1[CH:20]=[C:15]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)[N:16]=[C:17]([O:22][CH2:23][C:24]2[CH:28]=[CH:27][S:26][CH:25]=2)[CH:18]=1

参加物

6

反応物 4

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 199573902,4-Dichloro-6-(3-thienylmethyloxy)pyridine

生成物 1

HCID 199574124-Chloro-2-(3-thienylmethyloxy)-6-(meta-trifluoromethylphenoxy)pyridine

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

To a solution of meta-trifluoromethylphenol (0.28 g, 0.0018×1.0 mol) in 10 ml of dry N,N-dimethylacetamide, sodium hydride (0.077 g, (ca.60% in mineral oil), 0.0018×1.1 mol) was added. After the bubbling ceased, a solution of 2,4-dichloro-6-(3-thienylmethyloxy)pyridine (0.46 g, 0.0018 mol) in 10 ml of dry N,N-dimethylacetamide was added dropwise and the resultant solution was stirred for about 7 hours at the temperature of 160° to 170° C. After allowed to cool, water was added to the reaction solution, then the mixture was partitioned by using ethyl acetate. The obtained organic layer was washed with aqueous saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off, then the residue was purified successively on silica gel column chromatography and on reversed phase column chromatography (Lobar column, Lichroprep RP-18, 40-63 μm, elution solvent: CH3CN/H2O=7/3(v/v)), whereby the end product was obtained.

後処理

  1. temperatureto cool
  2. customthe mixture was partitioned
  3. washThe obtained organic layer was washed with aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified successively on silica gel column chromatography and on reversed phase column chromatography (Lobar column, Lichroprep RP-18, 40-63 μm, elution solvent: CH3CN/H2O=7/3(v/v)), whereby the end product
  7. customwas obtained

出典と根拠

ORDレコード
ord-52ac8f43bae54bb7b0d1b1fd35f86ba7
出典データセット
uspto-grants-1997_04
特許番号
US05624942

反応ノート

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